Acetic Acid → (2-Oxo-1,2-dihydro-indol-3-ylidene)-ethyl ethanoate

HRID 1969932Notes

Reaction equation

[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=O.N1CCCCC1.C(O)(=O)C.[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][C:19]1=[O:27]>C1(C)C=CC=CC=1.C(O)C>[C:1]([O:5][CH2:6][CH:7]=[C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:18][C:19]1=[O:27])(=[O:4])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

73.5 mL (360 mmol) of a 50% solution of ethyl glyoxalate in toluene then 3.6 ml, (36 mmol) of piperidine and 4.2 mL (72 mmol) of acetic acid are added to a solution of 24 g (180 mmol) of 1,3-dihydro-indol-2-one dissolved in 350 mL of ethanol. The reaction mixture is stirred at 70° C. for 20 hours then concentrated to a quarter by evaporation of the solvents under vacuum. The solid is filtered to give 18.3 g (47%) of (2-oxo-1,2-dihydro-indol-3-ylidene)-ethyl ethanoate in the form of an orange solid. The filtrate is evaporated, then recrystallized from ethanol to give an additional 2.7 g (7%) of (2-oxo-1,2-dihydro-indol-3-ylidene)-ethyl ethanoate in the form of an orange solid.

Workup

concentrationthen concentrated to a quarter by evaporation of the solvents under vacuum
filtrationThe solid is filtered

Sources & evidence

ORD record: ord-a88333fda8294785bb477adae061a66f
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426437B2

Reaction notes

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